ES2205239T3 - Compuestos mimeticos de g-csf no peptidicos. - Google Patents
Compuestos mimeticos de g-csf no peptidicos.Info
- Publication number
- ES2205239T3 ES2205239T3 ES97928663T ES97928663T ES2205239T3 ES 2205239 T3 ES2205239 T3 ES 2205239T3 ES 97928663 T ES97928663 T ES 97928663T ES 97928663 T ES97928663 T ES 97928663T ES 2205239 T3 ES2205239 T3 ES 2205239T3
- Authority
- ES
- Spain
- Prior art keywords
- bis
- imidazole
- octahydroimidazo
- pyridyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 127
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 title abstract description 35
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 title abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- -1 N-acylamino Chemical group 0.000 claims description 79
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 238000002360 preparation method Methods 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 14
- 208000004235 neutropenia Diseases 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 10
- 239000003981 vehicle Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 206010017533 Fungal infection Diseases 0.000 claims description 7
- 208000031888 Mycoses Diseases 0.000 claims description 7
- 150000002357 guanidines Chemical class 0.000 claims description 7
- 208000035143 Bacterial infection Diseases 0.000 claims description 6
- ULLPXRBZGJCVNL-UHFFFAOYSA-N N1=C(C=CC=C1)N1CNC2C1NCN2 Chemical compound N1=C(C=CC=C1)N1CNC2C1NCN2 ULLPXRBZGJCVNL-UHFFFAOYSA-N 0.000 claims description 6
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical class [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- AVUDGGYCULGPNJ-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydroimidazo[4,5-d]imidazole Chemical compound N1CNC2NCNC21 AVUDGGYCULGPNJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- VTCAPYWNMPEUDY-UHFFFAOYSA-N 2-n,5-n-bis(1h-benzimidazol-2-yl)-3a,6a-bis(6-methylpyridin-2-yl)-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound CC1=CC=CC(C23C(NC(N2)=NC=2NC4=CC=CC=C4N=2)(NC(N3)=NC=2NC3=CC=CC=C3N=2)C=2N=C(C)C=CC=2)=N1 VTCAPYWNMPEUDY-UHFFFAOYSA-N 0.000 claims description 3
- PCKFMHNRVMMOQI-UHFFFAOYSA-N 2-n,5-n-bis(1h-benzimidazol-2-yl)-3a,6a-bis[4-(trifluoromethyl)phenyl]-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N1)(NC(N2)=NC=3NC4=CC=CC=C4N=3)C2(C=2C=CC(=CC=2)C(F)(F)F)NC1=NC1=NC2=CC=CC=C2N1 PCKFMHNRVMMOQI-UHFFFAOYSA-N 0.000 claims description 3
- PCDSBNXNTDTPKY-UHFFFAOYSA-N 2-n,5-n-bis(1h-benzimidazol-2-yl)-3a,6a-diphenyl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N1C(=NC=2NC3=CC=CC=C3N=2)NC2(C=3C=CC=CC=3)NC(=NC=3NC4=CC=CC=C4N=3)NC12C1=CC=CC=C1 PCDSBNXNTDTPKY-UHFFFAOYSA-N 0.000 claims description 3
- DHYXCTSDXUOXGE-UHFFFAOYSA-N 2-n,5-n-bis(1h-benzimidazol-2-yl)-3a,6a-dipyridin-2-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N1C(=NC=2NC3=CC=CC=C3N=2)NC2(C=3N=CC=CC=3)NC(=NC=3NC4=CC=CC=C4N=3)NC12C1=CC=CC=N1 DHYXCTSDXUOXGE-UHFFFAOYSA-N 0.000 claims description 3
- IOPGGYVGILHEKV-UHFFFAOYSA-N 2-n,5-n-bis(1h-benzimidazol-2-yl)-3a-(3-chlorophenyl)-6a-phenyl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound ClC1=CC=CC(C23C(NC(N2)=NC=2NC4=CC=CC=C4N=2)(NC(N3)=NC=2NC3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 IOPGGYVGILHEKV-UHFFFAOYSA-N 0.000 claims description 3
- NEXUUGLNYYBRSC-UHFFFAOYSA-N 2-n,5-n-bis(1h-benzimidazol-2-yl)-6a-(2-chlorophenyl)-3a-phenyl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound ClC1=CC=CC=C1C(N1)(NC(N2)=NC=3NC4=CC=CC=C4N=3)C2(C=2C=CC=CC=2)NC1=NC1=NC2=CC=CC=C2N1 NEXUUGLNYYBRSC-UHFFFAOYSA-N 0.000 claims description 3
- HRJWOUWKSBOEFB-UHFFFAOYSA-N 2-n,5-n-bis(4-methyl-1h-benzimidazol-2-yl)-3a,6a-dipyridin-2-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N=1C=2C(C)=CC=CC=2NC=1NC(N1)=NC2(C=3N=CC=CC=3)N=C(NC=3NC4=CC=CC(C)=C4N=3)NC21C1=CC=CC=N1 HRJWOUWKSBOEFB-UHFFFAOYSA-N 0.000 claims description 3
- MLKMFVLWTZTCMD-UHFFFAOYSA-N 2-n,5-n-bis(6-fluoro-1h-benzimidazol-2-yl)-3a,6a-dipyridin-2-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N1C2=CC(F)=CC=C2N=C1NC(N1)=NC2(C=3N=CC=CC=3)N=C(NC=3NC4=CC(F)=CC=C4N=3)NC21C1=CC=CC=N1 MLKMFVLWTZTCMD-UHFFFAOYSA-N 0.000 claims description 3
- FIWJVYHSHZESGP-UHFFFAOYSA-N 2-n,5-n-bis(6-methyl-1h-benzimidazol-2-yl)-3a,6a-dipyridin-2-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N1C2=CC(C)=CC=C2N=C1N=C(N1)NC2(C=3N=CC=CC=3)NC(=NC=3NC4=CC(C)=CC=C4N=3)NC21C1=CC=CC=N1 FIWJVYHSHZESGP-UHFFFAOYSA-N 0.000 claims description 3
- BTARJFJDVRWALI-UHFFFAOYSA-N 2-n-(1h-benzimidazol-2-yl)-5-n-(6-methyl-1h-benzimidazol-2-yl)-3a,6a-dipyridin-2-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N1C2=CC(C)=CC=C2N=C1NC(N1)=NC2(C=3N=CC=CC=3)N=C(NC=3NC4=CC=CC=C4N=3)NC21C1=CC=CC=N1 BTARJFJDVRWALI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- BHSDTPZEWAAJSJ-UHFFFAOYSA-N 2-n,5-n-bis(1h-benzimidazol-2-yl)-3a,6a-bis(4-bromophenyl)-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound C1=CC(Br)=CC=C1C(N1)(NC(N2)=NC=3NC4=CC=CC=C4N=3)C2(C=2C=CC(Br)=CC=2)NC1=NC1=NC2=CC=CC=C2N1 BHSDTPZEWAAJSJ-UHFFFAOYSA-N 0.000 claims description 2
- WVRAGZNIRBQTAK-UHFFFAOYSA-N 2-n,5-n-bis(1h-benzimidazol-2-yl)-3a-phenyl-6a-pyridin-2-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N1C(=NC=2NC3=CC=CC=C3N=2)NC2(C=3N=CC=CC=3)NC(=NC=3NC4=CC=CC=C4N=3)NC12C1=CC=CC=C1 WVRAGZNIRBQTAK-UHFFFAOYSA-N 0.000 claims description 2
- HGMHMLORVIGINX-UHFFFAOYSA-N 2-n,5-n-bis(1h-benzimidazol-2-yl)-3a-phenyl-6a-pyridin-4-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N1C(=NC=2NC3=CC=CC=C3N=2)NC2(C=3C=CN=CC=3)NC(=NC=3NC4=CC=CC=C4N=3)NC12C1=CC=CC=C1 HGMHMLORVIGINX-UHFFFAOYSA-N 0.000 claims description 2
- WMVHEVDQQHCKEA-UHFFFAOYSA-N 2-n,5-n-bis(4-methyl-1,3-thiazol-2-yl)-3a,6a-dipyridin-2-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound CC1=CSC(NC=2NC3(NC(NC=4SC=C(C)N=4)=NC3(N=2)C=2N=CC=CC=2)C=2N=CC=CC=2)=N1 WMVHEVDQQHCKEA-UHFFFAOYSA-N 0.000 claims description 2
- IRMMGKOXRVXBTK-UHFFFAOYSA-N 2-n,5-n-bis(6-chloro-1h-benzimidazol-2-yl)-3a,6a-dipyridin-2-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N1C2=CC(Cl)=CC=C2N=C1N=C(N1)NC2(C=3N=CC=CC=3)NC(=NC=3NC4=CC(Cl)=CC=C4N=3)NC21C1=CC=CC=N1 IRMMGKOXRVXBTK-UHFFFAOYSA-N 0.000 claims description 2
- VYBWXUNMXKHLTQ-UHFFFAOYSA-N 2-n,5-n-bis(6-nitro-1h-benzimidazol-2-yl)-3a,6a-dipyridin-2-yl-1,6-dihydroimidazo[4,5-d]imidazole-2,5-diamine Chemical compound N1C2=CC([N+](=O)[O-])=CC=C2N=C1N=C(N1)NC2(C=3N=CC=CC=3)NC(=NC=3NC4=CC(=CC=C4N=3)[N+]([O-])=O)NC21C1=CC=CC=N1 VYBWXUNMXKHLTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
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- 239000003054 catalyst Substances 0.000 claims description 2
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- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
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- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 108
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- 239000000203 mixture Substances 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- JJWCTKUQWXYIIU-UHFFFAOYSA-N 2-Benzimidazolylguanidine Chemical compound C1=CC=C2NC(N=C(N)N)=NC2=C1 JJWCTKUQWXYIIU-UHFFFAOYSA-N 0.000 description 22
- PIINXYKJQGMIOZ-UHFFFAOYSA-N 1,2-dipyridin-2-ylethane-1,2-dione Chemical group C=1C=CC=NC=1C(=O)C(=O)C1=CC=CC=N1 PIINXYKJQGMIOZ-UHFFFAOYSA-N 0.000 description 20
- 239000000843 powder Substances 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1954296P | 1996-05-22 | 1996-05-22 | |
| US19542P | 1996-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2205239T3 true ES2205239T3 (es) | 2004-05-01 |
Family
ID=21793762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES97928663T Expired - Lifetime ES2205239T3 (es) | 1996-05-22 | 1997-05-22 | Compuestos mimeticos de g-csf no peptidicos. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5981551A (cs) |
| EP (1) | EP0920314B1 (cs) |
| JP (1) | JP2000512629A (cs) |
| KR (1) | KR20000015881A (cs) |
| AT (1) | ATE247959T1 (cs) |
| AU (1) | AU722453B2 (cs) |
| BR (1) | BR9709326A (cs) |
| CA (1) | CA2255731A1 (cs) |
| CZ (1) | CZ376798A3 (cs) |
| DE (1) | DE69724438T2 (cs) |
| ES (1) | ES2205239T3 (cs) |
| IL (1) | IL127065A0 (cs) |
| NO (1) | NO985406D0 (cs) |
| NZ (1) | NZ332823A (cs) |
| PL (1) | PL330148A1 (cs) |
| TR (1) | TR199802401T2 (cs) |
| WO (1) | WO1997044033A1 (cs) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7655699B1 (en) | 1992-04-22 | 2010-02-02 | Eisai Inc. | Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors |
| ES2284217T3 (es) | 1997-10-31 | 2007-11-01 | Smithkline Beecham Corporation | Complejos metalicos novedosos. |
| DE69839191T2 (de) * | 1997-10-31 | 2009-02-19 | Smithkline Beecham Corp. | Metall-komplexe mit antibakteriele und fungizide wirkungen |
| CA2328252A1 (en) * | 1998-04-14 | 1999-10-21 | Katherine Louisa Widdowson | Receptor ligands |
| TWI242563B (en) * | 1998-04-30 | 2005-11-01 | Tanox Inc | Monoclonal agonist antibodies which specifically bind to or interact with human G-CSF receptor |
| CA2332318A1 (en) * | 1998-05-22 | 1999-12-02 | Juan I. Luengo | G-csf mimetics |
| AU752272B2 (en) | 1998-05-22 | 2002-09-12 | Smithkline Beecham Corporation | G-CSF mimetics |
| JP2002167378A (ja) | 2000-09-22 | 2002-06-11 | Ss Pharmaceut Co Ltd | イミダゾール誘導体又はその塩 |
| US20050084908A1 (en) * | 2000-11-06 | 2005-04-21 | Chugai Seiyaku Kabushiki Kaisha | Methods for detecting binding of low-molecular-weight compound and its binding partner molecule |
| US7084070B1 (en) | 2001-03-30 | 2006-08-01 | Lam Research Corporation | Treatment for corrosion in substrate processing |
| US20020177321A1 (en) * | 2001-03-30 | 2002-11-28 | Li Si Yi | Plasma etching of silicon carbide |
| KR101010905B1 (ko) | 2002-01-18 | 2011-01-25 | 아스텔라스세이야쿠 가부시키가이샤 | 2-아실아미노티아졸 유도체 또는 그 염 |
| JP2006347882A (ja) * | 2003-09-02 | 2006-12-28 | Ss Pharmaceut Co Ltd | ベンジルアルコール誘導体又はその塩 |
| US20090226397A1 (en) * | 2003-10-24 | 2009-09-10 | Nora Therapeutics, Inc. | Compositions and methods for reducing the likelihood of implantation failure or miscarriage in recipients of artificial insemination |
| US8338373B2 (en) * | 2003-10-24 | 2012-12-25 | Nora Therapeutics, Inc. | Method for reducing the risk of spontaneous abortion in a human female subject |
| ES2405506T3 (es) | 2003-10-24 | 2013-05-31 | Nora Therapeutics, Inc. | Un método para obtener datos útiles en la identificación de un paciente con riesgo de tener dificultad de llevar a término un embarazo |
| US9216206B2 (en) | 2008-07-22 | 2015-12-22 | Menogenix, Inc. | Methods of treating symptoms associated with menopause and hormonal variations with G-CSF |
| US9151289B2 (en) | 2008-08-21 | 2015-10-06 | Cummins Inc. | Fuel pump |
| CZ302068B6 (cs) * | 2009-07-28 | 2010-09-22 | Univerzita Pardubice | Zpusob prípravy cis-1,3,4,6-tetranitrooktahydroimidazo-[4,5-d]imidazolu |
| WO2015057724A1 (en) | 2013-10-14 | 2015-04-23 | Nora Therapeutics, Inc. | Use of g-csf for treating or preventing villitis of unknown etiology in a human female |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2596126A (en) * | 1943-02-24 | 1952-05-13 | Homer W Carhart | Method for separating diaryl-2-imino hydantoins from the corresponding 2,5-di-imino glycolurils |
| JPS4995992A (cs) * | 1973-01-27 | 1974-09-11 | ||
| GB9120304D0 (en) * | 1991-09-24 | 1991-11-06 | Erba Carlo Spa | Stable pharmaceutical compositions containing a granulocyte macrophage colony stimulating factor |
-
1997
- 1997-05-22 AU AU32865/97A patent/AU722453B2/en not_active Expired
- 1997-05-22 DE DE69724438T patent/DE69724438T2/de not_active Expired - Lifetime
- 1997-05-22 CA CA002255731A patent/CA2255731A1/en not_active Abandoned
- 1997-05-22 KR KR1019980709432A patent/KR20000015881A/ko not_active Withdrawn
- 1997-05-22 WO PCT/US1997/008864 patent/WO1997044033A1/en active IP Right Grant
- 1997-05-22 PL PL97330148A patent/PL330148A1/xx unknown
- 1997-05-22 JP JP09542808A patent/JP2000512629A/ja not_active Ceased
- 1997-05-22 NZ NZ332823A patent/NZ332823A/xx not_active IP Right Cessation
- 1997-05-22 ES ES97928663T patent/ES2205239T3/es not_active Expired - Lifetime
- 1997-05-22 BR BR9709326A patent/BR9709326A/pt active Search and Examination
- 1997-05-22 US US09/194,217 patent/US5981551A/en not_active Expired - Lifetime
- 1997-05-22 CZ CZ983767A patent/CZ376798A3/cs unknown
- 1997-05-22 AT AT97928663T patent/ATE247959T1/de not_active IP Right Cessation
- 1997-05-22 TR TR1998/02401T patent/TR199802401T2/xx unknown
- 1997-05-22 EP EP97928663A patent/EP0920314B1/en not_active Expired - Lifetime
- 1997-05-22 IL IL12706597A patent/IL127065A0/xx unknown
-
1998
- 1998-11-20 NO NO985406A patent/NO985406D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69724438T2 (de) | 2004-06-09 |
| DE69724438D1 (de) | 2003-10-02 |
| EP0920314A4 (en) | 2001-08-16 |
| AU722453B2 (en) | 2000-08-03 |
| NZ332823A (en) | 2000-05-26 |
| BR9709326A (pt) | 1999-08-10 |
| IL127065A0 (en) | 1999-09-22 |
| EP0920314B1 (en) | 2003-08-27 |
| NO985406L (no) | 1998-11-20 |
| CZ376798A3 (cs) | 1999-04-14 |
| TR199802401T2 (xx) | 1999-03-22 |
| US5981551A (en) | 1999-11-09 |
| JP2000512629A (ja) | 2000-09-26 |
| WO1997044033A1 (en) | 1997-11-27 |
| NO985406D0 (no) | 1998-11-20 |
| CA2255731A1 (en) | 1997-11-27 |
| KR20000015881A (ko) | 2000-03-15 |
| ATE247959T1 (de) | 2003-09-15 |
| PL330148A1 (en) | 1999-04-26 |
| EP0920314A1 (en) | 1999-06-09 |
| AU3286597A (en) | 1997-12-09 |
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